EP0761721A2 - Procédé pour la préparation de poly-o-hydroxyamides et de poly-o-mercaptoamides - Google Patents

Procédé pour la préparation de poly-o-hydroxyamides et de poly-o-mercaptoamides Download PDF

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Publication number
EP0761721A2
EP0761721A2 EP96113308A EP96113308A EP0761721A2 EP 0761721 A2 EP0761721 A2 EP 0761721A2 EP 96113308 A EP96113308 A EP 96113308A EP 96113308 A EP96113308 A EP 96113308A EP 0761721 A2 EP0761721 A2 EP 0761721A2
Authority
EP
European Patent Office
Prior art keywords
poly
bis
dicarboxylic acid
hydroxyamides
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP96113308A
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German (de)
English (en)
Other versions
EP0761721B1 (fr
EP0761721A3 (fr
Inventor
Recai Dr. Sezi
Hellmut Dr. Ahne
Eberhard Kühn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Infineon Technologies AG
Original Assignee
Siemens AG
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Filing date
Publication date
Application filed by Siemens AG filed Critical Siemens AG
Publication of EP0761721A2 publication Critical patent/EP0761721A2/fr
Publication of EP0761721A3 publication Critical patent/EP0761721A3/fr
Application granted granted Critical
Publication of EP0761721B1 publication Critical patent/EP0761721B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0683—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0666—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0677—Polycondensates containing five-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/08—Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/18—Polybenzimidazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/22—Polybenzoxazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/32—Polythiazoles; Polythiadiazoles
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides

Definitions

  • the invention relates to a process for the preparation of poly-o-hydroxyamides (polybenzoxazole precursors) and poly-o-mercaptoamides (polybenzothiazole precursors).
  • Highly heat-resistant polymers are required in microelectronics, in particular as protective and insulating layers or as dielectrics (see, for example: "SAMPE Journal", Vol. 25 (1989), No. 6, pages 18 to 23, and “Proceedings of the 1992 International Conference on Multichip Modules “, pages 394 to 400).
  • Some of the polymers used for example homo- and copolymers of aromatic polyethers and precursors of polyimides (PI) and polybenzoxazoles (PBO), have good solubility in organic solvents and good film-forming properties and can be applied to electronic components by means of centrifugal technology (see for example: “High Performance Polymers", Vol. 4 (1992), No. 2, pages 73 to 80, and “Polymers for Advanced Technologies", Vol. 4 (1993), pages 217 to 233).
  • PI polyimides
  • PBO polybenzoxazoles
  • Polymer precursors of the type mentioned are cyclized by a temperature treatment, ie converted into the corresponding polymers (PI or PBO); this gives the final properties. Because of the cyclization, the hydrophilic groups of the poly-o-hydroxyamide, ie the NH, OH and CO groups, which would have a negative effect on the dielectric properties and water absorption, disappear. This is, for example, an essential advantage of the polybenzoxazoles over the polyimides (with two CO groups per imide unit) and in particular over the hydroxypolyimides (with two CO groups and one OH group per imide unit). In addition, the cyclization is not only for the good dielectric properties and the low Water absorption of the end product is important, but also for its high temperature stability.
  • PI and PBO precursors can be photosensitive, for example by adding suitable photoactive components, and then structured directly, i.e. without the use of an auxiliary resist. This is important because direct structuring - compared to indirect structuring - offers considerable cost advantages.
  • photosensitive PBO precursors offer the advantages of positive structurability, such as a lower defect density when structuring the so-called "via holes" because, compared to negative-working systems, only a fraction of the area is exposed becomes.
  • alkali-soluble PBO precursors there is also the possibility of aqueous alkaline development. After the photostructuring, the cyclization of the precursors takes place by tempering.
  • Aqueous-alkaline PBO precursors are already known (see: EP-PS 0 023 662, EP-OS 0 264 678 and EP-PS 0 291 779).
  • the photolithographic process used, apart from the cyclization, is the same as in the structuring of known positive resists based on novolaks and quinone azides, a process used in numerous production lines worldwide (see for example: DS Soane and Z. Martynenko "Polymers in Microelectronics - Fundamentals and Applications ", Elsevier, Amsterdam 1989, pages 77 to 124).
  • the alkali solubility of the PBO precursors is an important prerequisite for their use as a base polymer for photosensitive dielectrics which can be developed in aqueous alkaline.
  • the precursors must be soluble in developers free of metal ions so that such developers are also used in photostructuring can. Developers that contain metal ions can adversely affect the electrical function of the components.
  • alkali-soluble PBO precursors i.e. of poly-o-hydroxyamides
  • a suitable bis-o-aminophenol a suitable bis-o-aminophenol.
  • a soluble base such as pyridine, is generally added to trap the hydrogen chloride formed in the reaction (see: EP-OS 0 264 678 and EP-PS 0 291 779).
  • the requirement must also be met that the dicarboxylic acid chloride predominantly reacts with the amino groups of bis-o-aminophenol (with amide formation), but not with its hydroxyl groups (with ester formation), ie the reaction selectivity of amide formation compared to the ester formation must be high. If the ester formation cannot be excluded or strongly suppressed, this leads to insufficiently alkali-soluble polymers. A low reaction selectivity can also lead to gel formation in the polymer solution, the poly-o-hydroxyamide produced then being unfilterable and thus unusable.
  • An alternative chloride-free production process for poly-o-hydroxyamides consists in reacting the dicarboxylic acid with the bis-o-aminophenol using condensation reagents such as 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline and 1,1'-carbonyldioxy-di-1 To use 2,3-benzotriazole (see: EP-OS 0 391 196).
  • condensation reagents such as 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline and 1,1'-carbonyldioxy-di-1
  • 2,3-benzotriazole see: EP-OS 0 391 196.
  • the polymers produced in this way also show an insufficient solubility in metal-ion-free aqueous alkaline developers.
  • the object of the invention is to provide a cost-effective method with which - by a chloride-free route - poly-o-hydroxyamides and poly-o-mercaptoamides can be produced which are soluble in metal-ion-free aqueous alkaline developers.
  • the invention solves the problem described above in such a way that special dicarboxylic acid derivatives are used as the dicarboxylic acid component, namely fluorine-containing esters with phenols or corresponding thioesters and amides. Surprisingly, this results in a sufficient selectivity of the amide formation.
  • the polymers made according to the invention i.e. the poly-o-hydroxy- and poly-o-mercaptoamides, namely, are soluble in metal-ion-free aqueous alkaline developers.
  • the process according to the invention proceeds without gel formation, so that the polymers mentioned are readily soluble and processable in organic solvents. This method also prevents contamination such as chloride and metal ions and phosphorus compounds.
  • dicarboxylic acids such as 1,3-benzenedicarboxylic acid (isophthalic acid) and diphenyl ether-4,4'-dicarboxylic acid (oxydibenzoic acid) are preferably used for the synthesis of the precursors.
  • dicarboxylic acids which are used for the preparation of precursors of the type mentioned.
  • Particularly suitable bis-o-aminophenols are 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane and 3,3'-dihydroxy-4,4'-diaminodiphenyl.
  • the corresponding bis-o-aminothiophenols are used for the synthesis of poly-o-mercaptoamides.
  • all bis-o-aminophenols and thiophenols can be used which are usually used for the preparation of polybenzoxazole or polybenzothiazole precursors.
  • the reaction of the dicarboxylic acid derivative with the bis (thio) phenol is advantageously carried out in the presence of a basic catalyst, which is preferably a tertiary amine.
  • a basic catalyst which is preferably a tertiary amine.
  • Such catalysts are, in particular, pyridine, triethylamine, diazabicyclooctane and polyvinylpyridine.
  • other basic catalysts can also be used, preference being given to those which are readily soluble in the solvent used in the synthesis of the precursor, such as N-methylpyrrolidone, or in water or water / alcohol mixtures (precipitant), or such which are completely insoluble, such as cross-linked polyvinyl pyridine.
  • the reaction temperature in the reaction between the dicarboxylic acid derivative and the (thio) phenol is preferably between 20 and 150 ° C.
  • the reaction selectivity it has proven to be advantageous to increase the temperature in stages.
  • the process according to the invention is therefore advantageously carried out in such a way that the dicarboxylic acid derivative, the bis-o-aminophenol or -thiophenol and a basic catalyst are dissolved in an organic solvent at room temperature, if appropriate at elevated temperature, and then in stages is heated. After the reaction has ended, the reaction solution is allowed to cool to room temperature, then the reaction product is precipitated with a suitable precipitant. After filtration and drying, the precipitated polymer is ready for use. In the method according to the invention, cumbersome cleaning steps, such as cleaning the polymer by means of ion exchangers, are therefore unnecessary.
  • Suitable solvents are also N-methylpyrrolidone, tetrahydrofuran and N, N-dimethylacetamide. In principle, however, any solvent in which the starting components are readily soluble can be used. Water and mixtures of water with alcohols such as ethanol and isopropanol are particularly suitable as precipitants.
  • the amino end groups of the poly-o-hydroxyamide or mercaptoamide produced can be capped with a dicarboxylic anhydride before the polymer precipitates, i.e. be blocked.
  • a dicarboxylic anhydride for this purpose, cis-5-norbornene-endo-2,3-dicarboxylic anhydride is particularly suitable.
  • Example 2 If the PBO precursor prepared according to Example 4 is used as in Example 2, the same result is obtained, i.e. the PBO precursor dissolves uniformly in both metal-ion-free aqueous alkaline developers.
  • Example 3 If the PBO precursor prepared according to Example 4 is used as in Example 3, the same result is obtained, i.e. only the exposed areas are selectively and evenly detached.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Polyamides (AREA)
EP96113308A 1995-08-31 1996-08-19 Procédé pour la préparation de poly-o-hydroxyamides et de poly-o-mercaptoamides Expired - Lifetime EP0761721B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19532200 1995-08-31
DE19532200 1995-08-31

Publications (3)

Publication Number Publication Date
EP0761721A2 true EP0761721A2 (fr) 1997-03-12
EP0761721A3 EP0761721A3 (fr) 1997-05-02
EP0761721B1 EP0761721B1 (fr) 2001-02-28

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EP96113308A Expired - Lifetime EP0761721B1 (fr) 1995-08-31 1996-08-19 Procédé pour la préparation de poly-o-hydroxyamides et de poly-o-mercaptoamides

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Country Link
US (1) US5922825A (fr)
EP (1) EP0761721B1 (fr)
JP (1) JP3167629B2 (fr)
DE (1) DE59606489D1 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3973730B2 (ja) * 1997-05-06 2007-09-12 富士ゼロックス株式会社 帯電付与部材とその製造方法、それを用いた静電潜像現像剤、画像形成装置及び画像形成方法
US20050032351A1 (en) * 1998-12-21 2005-02-10 Mou-Shiung Lin Chip structure and process for forming the same
DE10145471A1 (de) * 2001-09-14 2003-04-17 Infineon Technologies Ag Fotosensitive Formulierung für Pufferschichten und Verwendungen dazu
DE10145469B4 (de) * 2001-09-14 2006-07-06 Infineon Technologies Ag Poly-o-hydroxyamid und Verfahren zu seiner Weiterverarbeitung zu Polybenzoxazol
DE10145472A1 (de) * 2001-09-14 2003-04-17 Infineon Technologies Ag Fotosensitive Formulierung für Pufferschichten und Verwendungen dazu
US6798073B2 (en) 2001-12-13 2004-09-28 Megic Corporation Chip structure and process for forming the same
WO2004109400A2 (fr) * 2003-03-11 2004-12-16 Arch Speciality Chemicals, Inc. Nouvelles compositions de resine photosensible
KR20060004908A (ko) * 2003-03-11 2006-01-16 후지필름 일렉트로닉 머티리얼스 유.에스.에이., 아이엔씨. 새로운 감광성 수지 조성물들
KR20060002768A (ko) * 2003-03-11 2006-01-09 후지필름 일렉트로닉 머티리얼스 유.에스.에이., 아이엔씨. 새로운 감광성 수지 조성물들
KR20060002751A (ko) * 2003-03-11 2006-01-09 후지필름 일렉트로닉 머티리얼스 유.에스.에이., 아이엔씨. 새로운 감광성 수지 조성물들

Citations (1)

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Publication number Priority date Publication date Assignee Title
FR2595362A1 (fr) * 1986-03-06 1987-09-11 Central Glass Co Ltd Polyamides et polybenzoxazoles aromatiques ayant des unites de diphenylhexafluoropropane, et leur procede de preparation

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DE2901843A1 (de) * 1979-01-18 1980-07-31 Hoechst Ag Verfahren zur herstellung von carbonsaeureamiden und peptiden
DE2931297A1 (de) * 1979-08-01 1981-02-19 Siemens Ag Waermebestaendige positivresists und verfahren zur herstellung waermebestaendiger reliefstrukturen
DE3411659A1 (de) * 1984-03-29 1985-10-03 Siemens AG, 1000 Berlin und 8000 München Verfahren zur herstellung von polyoxazol- und polythiazol-vorstufen
US5021320A (en) * 1986-10-02 1991-06-04 Hoechst Celanese Corporation Polyamide containing the hexafluoroisopropylidene group with O-quinone diazide in positive working photoresist
EP0264678B1 (fr) * 1986-10-02 1991-09-18 Hoechst Celanese Corporation Polyamides contenant des groupes hexafluoroisopropylène, compositions photosensibles positives les contenant et matériaux d'enregistrement les utilisant
DE3850809D1 (de) * 1987-05-18 1994-09-01 Siemens Ag Wärmebeständige Positivresists und Verfahren zur Herstellung wärmebeständiger Reliefstrukturen.
DE3716629C2 (de) * 1987-05-18 1997-06-12 Siemens Ag Wärmebeständige positiv arbeitende strahlungsempfindliche Gemische und Verfahren zur Herstellung wärmebeständiger Reliefstrukturen
US5037720A (en) * 1987-07-21 1991-08-06 Hoechst Celanese Corporation Hydroxylated aromatic polyamide polymer containing bound naphthoquinone diazide photosensitizer, method of making and use
EP0391196A3 (fr) * 1989-04-06 1991-02-27 Siemens Aktiengesellschaft Production de polyamides contenant des groupes hydroxy
JP3123144B2 (ja) * 1990-10-19 2001-01-09 東洋紡績株式会社 ポリベンゾアゾールポリマーの段階重合方法
US5194568A (en) * 1990-10-19 1993-03-16 The Dow Chemical Company Staged polymerization of polybenzazole polymers
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Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
FR2595362A1 (fr) * 1986-03-06 1987-09-11 Central Glass Co Ltd Polyamides et polybenzoxazoles aromatiques ayant des unites de diphenylhexafluoropropane, et leur procede de preparation

Also Published As

Publication number Publication date
US5922825A (en) 1999-07-13
EP0761721B1 (fr) 2001-02-28
EP0761721A3 (fr) 1997-05-02
JP3167629B2 (ja) 2001-05-21
DE59606489D1 (de) 2001-04-05
JPH09183847A (ja) 1997-07-15

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